CN1314320C - Method for preparing organosilyl quaternary ammonium salt sterilizing agent - Google Patents
Method for preparing organosilyl quaternary ammonium salt sterilizing agent Download PDFInfo
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- CN1314320C CN1314320C CNB2005100452940A CN200510045294A CN1314320C CN 1314320 C CN1314320 C CN 1314320C CN B2005100452940 A CNB2005100452940 A CN B2005100452940A CN 200510045294 A CN200510045294 A CN 200510045294A CN 1314320 C CN1314320 C CN 1314320C
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- quaternary ammonium
- ammonium salt
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- ethyl alcohol
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Abstract
The present invention discloses a preparation method of organic silicon quaternary ammonium salt germicide. The present invention has the steps that anhydrous sodium sulfate is dewatered; the anhydrous sodium sulfate is added in anhydrous alcohol to be stirred to prepare the anhydrous alcohol which is dewatered completely for standby; dimethyl octadecalamine are added in the anhydrous alcohol which is dewatered completely to be stirred until the dimethyl octadecalamine is dissolved, and then, gamma-chloropropyl triethoxysilane is dropped slowly to be stirred uniformly; the catalyst is added to have temperature reaction, after the 70 hour reaction, the Cl-content is measured once every five hours, and the complete degree of the reaction is calculated by taking the dimethyl octadecalamine as reference; the reaction is completed when reaching 98% and carries out continuously for 10 hours to obtain the organic silicon quaternary ammonium salt, the room temperature is lowered, and the pH of the organic silicon quaternary ammonium salt is adjusted to 7 by glacial acetic acid and is counted by weight percentage; the concentration of the organic silicon quaternary ammonium salt is adjusted to 40% by the anhydrous alcohol which is dewatered completely to obtain the organic silicon quaternary ammonium salt germicide. The method of the present invention has simple technology, low raw material price, easy raw material acquisition, high purity and high output, and the present invention is suitable for industrial production.
Description
Technical field
The present invention relates to the preparation method of a kind of sterilization, relate in particular to a kind of preparation method of organosilicon quaternary ammonium salt bactericide, belong to field of fine chemical with chemicals.
Background technology
At present, domestic sterilization of using has many kinds with chemicals, each have their own advantage and characteristics.Alkyl quaternary ammonium salts is the cationic surfactant of a quasi-representative, has very strong restraining and sterilizing bacteria effect, is widely used in the disinfection of public place such as hospital, swimming pool, algae is killed in the sterilization of recirculated cooling water, is used as oil field bactericide, water shutoff agent in a large number.But alkyl quaternary ammonium salts has very big weakness: chemism is low, and being applied on the textile is dissolution type, easily wash-out; Its toxicity is relatively large, and easily in the enrichment gradually of human body skin surface, the long-term use is easy to generate pathology.And the excitant of alkyl quaternary ammonium salts is stronger, and range of application is restricted.
The antibiotic mechanism of quarternary ammonium salt compound is as follows: quaternary ammonium salt has a center of positive charge [N
+], under electric field effects, the metabolic function torpescence of ferment in the cell membrane, respiratory function is damaged, and by the infiltration diffusion, changes the cell permeability, destroy the cell membrane cell wall, suppress the synzyme of nucleic acid and protein, it is deadly finally to cause the cell Dissolve things inside to leach.
The organosilicon quaternary ammonium salt bactericide is by alkyl-modified on the siloxanes substituted alkyl quaternary ammonium salt and the compound that obtains, it is a kind of cationic surfactant, very wide hydrophile-lipophile balance value (HLB value) is arranged, its chemism improves greatly, can react with the active group of matrix, combination closely forms firm film each other with it.Organosilicon quaternary ammonium salt series bactericidal agent restraining and sterilizing bacteria scope is wide, and Staphylococcus aureus, Escherichia coli, hepatitis B surface antigen, salmonella typhi, shigella dysenteriae and gonococcus etc. are had good killing effect.The organosilicon quaternary ammonium salt series bactericidal agent also has very high safety, and its half lethal dose is: LD
50＞10g/Kg.Can be used as the sterilization of family and household supplies, and industrial bactericide.
In view of the organosilicon quaternary ammonium salt bactericide has good prospects for application, adopt the preparation method that synthetic route is short, synthesis technique is simple, cost of material is low, environmental pollution is little, the organosilicon quaternary ammonium salt bactericide is accomplished scale production, have realistic meaning.
DOW Corning company at eighties of last century the seventies just with structure is:
[(CH
3O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-Launch products, its trade names are: DC-5700, this product prove that through the performance test of strictness its safety is very high, and its half lethal dose is: LD
50=12.27g/Kg authenticates by EPA.But this product (DC-5700) will be done raw material and solvent with methyl alcohol, easily operating personnel is caused murder by poisoning, has also limited its application.
Summary of the invention
At the deficiencies in the prior art, the problem to be solved in the present invention provides a kind of preparation method of organosilicon quaternary ammonium salt bactericide, this method technology is easy, raw material is cheap and easy to get, and, overcome the weakness of DC-5700, effectively satisfied the organosilicon quaternary ammonium salt bactericide and produced needs, expanded range of application greatly.
The preparation method of a kind of organosilicon quaternary ammonium salt bactericide of the present invention, be made up of following step:
A. anhydrous sodium sulfate being placed temperature is 200 ± 10 ℃ of environment, dry 5 hours, dewaters;
B. the anhydrous sodium sulfate after will dewatering is anhydrous sodium sulfate with the weight ratio: absolute ethyl alcohol=5～10: 100 amount joins in the absolute ethyl alcohol, stirs 20～30 hours, and preparation is the absolute ethyl alcohol of dehydration fully, and is standby;
C. under 50～70 rev/mins mixing speed, dimethyl 18 tertiary amines are joined in the absolute ethyl alcohol of above-mentioned dehydration fully until its dissolving, and then slowly drip γ-chloropropyl triethoxysilane, and stir, the dropping time was controlled in 2 hours; Wherein, described each component mol ratio is dimethyl 18 tertiary amine C
18H
37N (CH
3)
2: γ-chloropropyl triethoxysilane ClC
3H
6Si (OC
2H
5)
3: absolute ethyl alcohol=1.0: 1.1～1.3: 7.0～8.0;
D. in the described solution of step C, be catalyzer: γ-chloropropyl triethoxysilane ClC with the weight ratio
3H
6Si (OC
2H
5)
3=2～5: 100 amount adds catalyzer, sealed reactor, and condenser water flowing work is warming up to 80～84 ℃, under the state of alcohol reflux, reacts 80～100 hours; Wherein said catalyzer is selected from potassium iodide, iodomethane or iodoethane;
E. after reaction 70 hours, measured once [Cl in per 5 hours
-] content, be benchmark with dimethyl 18 tertiary amines, calculate the degree that reacts completely, reaction is fully to 98%, continues reaction 10 hours, organosilicon quaternary ammonium salt, its structural formula is: [(CH
3CH
2O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-
F. cool to room temperature, transfer the pH to 7 of above-mentioned organosilicon quaternary ammonium salt, by weight percentage, transfer its concentration to 40%, promptly get the organosilicon quaternary ammonium salt bactericide with the above-mentioned absolute ethyl alcohol of dehydration fully with glacial acetic acid.
Wherein, anhydrous sodium sulfate described in the step B: absolute ethyl alcohol is preferably 7～9: 100, and described mixing time is preferably 23～25 hours.
Wherein, each component mol ratio is preferably dimethyl 18 tertiary amines described in the step C: γ-chloropropyl triethoxysilane: absolute ethyl alcohol=1.0: 1.2: 7.5.
In the preparation method of above-mentioned organosilicon quaternary ammonium salt bactericide, the preferred potassium iodide of the catalyzer described in the step D.
In the preparation method of above-mentioned a kind of organosilicon quaternary ammonium salt bactericide, γ-chloropropyl triethoxysilane is excessive in the described reaction of step e, because its high volatility, under the alcohol reflux situation, can volatilization remove, therefore after reacting completely, should continue to react 10 hours, make γ-chloropropyl triethoxysilane volatilization thorough.
Utilize method of the present invention to prepare the organosilicon quaternary ammonium salt bactericide, technology is easy, and raw material is cheap and easy to get, production equipment and environmental condition are less demanding, and output is big, is fit to very much large-scale industrial production, has realized the growth requirement of organosilicon quaternary ammonium salt bactericide production industry.In the organosilicon quaternary ammonium salt compound of the present invention's preparation three ethyoxyls are arranged, can make solvent with ethanol, this had both helped selecting raw material cheap and easy to get, overcome the murder by poisoning that methyl alcohol brings as solvent again, the reaction condition gentleness, the ethanolic solution of product is convenient to store, transports, packs and is used.
The preparation of organosilicon quaternary ammonium salt bactericide of the present invention can be used as the portable bactericide of travelling, and bath water bactericide, underwear bactericide, guest room fabric are with bactericide, indoor environment bactericide, home textile bactericide.
Because organosilicon quaternary ammonium salt has many one's best qualities, develops new more products, and is applied in the other field, and it is fully utilized, to increasing the bactericide kind, the safety that improves bactericide is significant.
Embodiment
The following example is that the invention will be further described, but the present invention is not limited only to this.
Embodiment 1: a kind of preparation method of organosilicon quaternary ammonium salt bactericide
Form by following step:
A. anhydrous sodium sulfate being placed temperature is 200 ℃ of environment, dry 5 hours, dewaters;
B. the anhydrous sodium sulfate after will dewatering is anhydrous sodium sulfate with the weight ratio: the amount of absolute ethyl alcohol=8: 100 joins in the absolute ethyl alcohol, stirs 24 hours, and preparation is the absolute ethyl alcohol of dehydration fully, and is standby;
C. under 60 rev/mins mixing speed, dimethyl 18 tertiary amines are joined in the absolute ethyl alcohol of above-mentioned dehydration fully until its dissolving, and then slowly drip γ-chloropropyl triethoxysilane, and stir, the dropping time was controlled in 2 hours; Wherein, described each component mol ratio is dimethyl 18 tertiary amine C
18H
37N (CH
3)
2: γ-chloropropyl triethoxysilane ClC
3H
6Si (OC
2H
5)
3: absolute ethyl alcohol=1.0: 1.2: 7.5;
D. in the described solution of step C, be catalyzer: γ-chloropropyl triethoxysilane ClC with the weight ratio
3H
6Si (OC
2H
5)
3=4.5: 100 amount adds the catalyzer potassium iodide, sealed reactor, and condenser water flowing work is warming up to 80～84 ℃, under the state of alcohol reflux, reacts 80～100 hours;
E. after reaction 70 hours, measured once [Cl in per 5 hours
-] content, be benchmark with dimethyl 18 tertiary amines, calculate the degree that reacts completely, reaction is fully to 98%, continues reaction 10 hours, organosilicon quaternary ammonium salt, its structural formula is: [(CH
3CH
2O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-
F. cool to room temperature, transfer the pH to 7 of above-mentioned organosilicon quaternary ammonium salt, by weight percentage, transfer its concentration to 40%, promptly get the organosilicon quaternary ammonium salt bactericide with the above-mentioned absolute ethyl alcohol of dehydration fully with glacial acetic acid.
In the preparation method of above-mentioned organosilicon quaternary ammonium salt bactericide, γ-chloropropyl triethoxysilane is excessive in the described reaction of step e, because its high volatility, under the alcohol reflux situation, can volatilization remove, therefore after reacting completely, should continue to react 10 hours, make γ-chloropropyl triethoxysilane volatilization thorough.
Embodiment 2: a kind of preparation method of organosilicon quaternary ammonium salt bactericide
Form by following step:
A. anhydrous sodium sulfate being placed temperature is 210 ℃ of environment, dry 5 hours, dewaters;
B. the anhydrous sodium sulfate after will dewatering is anhydrous sodium sulfate with the weight ratio: the amount of absolute ethyl alcohol=10: 100 joins in the absolute ethyl alcohol, stirs 30 hours, and preparation is the absolute ethyl alcohol of dehydration fully, and is standby;
C. under 50～70 rev/mins mixing speed, dimethyl 18 tertiary amines are joined in the absolute ethyl alcohol of above-mentioned dehydration fully until its dissolving, and then slowly drip γ-chloropropyl triethoxysilane, and stir, the dropping time was controlled in 2 hours; Wherein, described each component mol ratio is dimethyl 18 tertiary amine C
18H
37N (CH
3)
2: γ-chloropropyl triethoxysilane ClC
3H
6Si (OC
2H
5)
3: absolute ethyl alcohol=1.0: 1.3: 8.0;
D. in the described solution of step C, be catalyzer: γ-chloropropyl triethoxysilane ClC with the weight ratio
3H
6Si (OC
2H
5)
3=3.5: 100 amount adds the catalyzer iodoethane, sealed reactor, and condenser water flowing work is warming up to 80～84 ℃, under the state of alcohol reflux, reacts 80～100 hours;
E. after reaction 70 hours, measured once [Cl in per 5 hours
-] content, be benchmark with dimethyl 18 tertiary amines, calculate the degree that reacts completely, reaction is fully to 98%, continues reaction 10 hours, organosilicon quaternary ammonium salt, its structural formula is: [(CH
3CH
2O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-
F. cool to room temperature, transfer the pH to 7 of above-mentioned organosilicon quaternary ammonium salt, by weight percentage, transfer its concentration to 40%, promptly get the organosilicon quaternary ammonium salt bactericide with the above-mentioned absolute ethyl alcohol of dehydration fully with glacial acetic acid.
In the preparation method of above-mentioned a kind of organosilicon quaternary ammonium salt bactericide, γ-chloropropyl triethoxysilane is excessive in the described reaction of step e, because its high volatility, under the alcohol reflux situation, can volatilization remove, therefore after reacting completely, should continue to react 10 hours, make γ-chloropropyl triethoxysilane volatilization thorough.
Embodiment 3: a kind of preparation method of organosilicon quaternary ammonium salt bactericide
Form by following step:
A. anhydrous sodium sulfate being placed temperature is 190 ℃ of environment, dry 5 hours, dewaters;
B. the anhydrous sodium sulfate after will dewatering is anhydrous sodium sulfate with the weight ratio: the amount of absolute ethyl alcohol=5: 100 joins in the absolute ethyl alcohol, stirs 20 hours, and preparation is the absolute ethyl alcohol of dehydration fully, and is standby;
C. under 50～70 rev/mins mixing speed, dimethyl 18 tertiary amines are joined in the absolute ethyl alcohol of above-mentioned dehydration fully until its dissolving, and then slowly drip γ-chloropropyl triethoxysilane, and stir, the dropping time was controlled in 2 hours; Wherein, described each component mol ratio is dimethyl 18 tertiary amine C
18H
37N (CH
3)
2: γ-chloropropyl triethoxysilane ClC
3H
6Si (OC
2H
5)
3: absolute ethyl alcohol=1.0: 1.1: 7.0;
D. in the described solution of step C, be catalyzer: γ-chloropropyl triethoxysilane ClC with the weight ratio
3H
6Si (OC
2H
5)
3=2.5: 100 amount adds the catalyzer iodomethane, sealed reactor, and condenser water flowing work is warming up to 80～84 ℃, under the state of alcohol reflux, reacts 80～100 hours;
E. after reaction 70 hours, measured once [Cl in per 5 hours
-] content, be benchmark with dimethyl 18 tertiary amines, calculate the degree that reacts completely, reaction is fully to 98%, continues reaction 10 hours, organosilicon quaternary ammonium salt, its structural formula is: [(CH
3CH
2O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-
F. cool to room temperature, transfer the pH to 7 of above-mentioned organosilicon quaternary ammonium salt, by weight percentage, transfer its concentration to 40%, promptly get the organosilicon quaternary ammonium salt bactericide with the above-mentioned absolute ethyl alcohol of dehydration fully with glacial acetic acid.
In the preparation method of above-mentioned a kind of organosilicon quaternary ammonium salt bactericide, γ-chloropropyl triethoxysilane is excessive in the described reaction of step e, because its high volatility, under the alcohol reflux situation, can volatilization remove, therefore after reacting completely, should continue to react 10 hours, make γ-chloropropyl triethoxysilane volatilization thorough.
Claims (5)
1. the preparation method of an organosilicon quaternary ammonium salt bactericide, be made up of following step:
A. anhydrous sodium sulfate being placed temperature is 200 ± 10 ℃ of environment, dry 5 hours, dewaters;
B. the anhydrous sodium sulfate after will dewatering is anhydrous sodium sulfate with the weight ratio: absolute ethyl alcohol=5～10: 100 amount joins in the absolute ethyl alcohol, stirs 20～30 hours, and preparation is the absolute ethyl alcohol of dehydration fully, and is standby;
C. under 50～70 rev/mins mixing speed, dimethyl 18 tertiary amines are joined in the absolute ethyl alcohol of above-mentioned dehydration fully until its dissolving, and then slowly drip γ-chloropropyl triethoxysilane, and stir, the dropping time was controlled in 2 hours; Wherein, described each component mol ratio is dimethyl 18 tertiary amine C
18H
37N (CH
3)
2: γ-chloropropyl triethoxysilane ClC
3H
6Si (OC
2H
5)
3: absolute ethyl alcohol=1.0: 1.1～1.3: 7.0～8.0;
D. in the described solution of step C, be catalyzer: γ-chloropropyl triethoxysilane ClC with the weight ratio
3H
6Si (OC
2H
5)
3=2～5: 100 amount adds catalyzer, sealed reactor, and condenser water flowing work is warming up to 80 ℃, under the state of alcohol reflux, reacts 80～100 hours; Wherein said catalyzer is selected from potassium iodide, iodomethane or iodoethane;
E. after reaction 70 hours, measured once [Cl in per 5 hours
-] content, be benchmark with dimethyl 18 tertiary amines, calculate the degree that reacts completely, reaction is fully to 98%, continues reaction 10 hours, organosilicon quaternary ammonium salt, its structural formula is: [(CH
3CH
2O)
3Si (CH
2)
3N (CH
3)
2(C
18H
37)]
+Cl
-
F. cool to room temperature, transfer the pH to 7 of above-mentioned organosilicon quaternary ammonium salt, by weight percentage, transfer its concentration to 40%, promptly get the organosilicon quaternary ammonium salt bactericide with the above-mentioned absolute ethyl alcohol of dehydration fully with glacial acetic acid.
2. the preparation method of organosilicon quaternary ammonium salt bactericide as claimed in claim 1 is characterized in that, anhydrous sodium sulfate described in the step B: absolute ethyl alcohol=7～9: 100, and described mixing time is 23～25 hours.
3. the preparation method of organosilicon quaternary ammonium salt bactericide as claimed in claim 1 is characterized in that, each component mol ratio described in the step C is dimethyl 18 tertiary amines: γ-chloropropyl triethoxysilane: absolute ethyl alcohol=1.0: 1.2: 7.5.
4. the preparation method of organosilicon quaternary ammonium salt bactericide as claimed in claim 1 is characterized in that, the catalyzer described in the step D selects potassium iodide.
5. the preparation method of organosilicon quaternary ammonium salt bactericide as claimed in claim 1, it is characterized in that γ-chloropropyl triethoxysilane is excessive in the described reaction of step e, after reacting completely, should continue to react 10 hours, and make γ-chloropropyl triethoxysilane volatilization thorough.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100452940A CN1314320C (en) | 2005-11-30 | 2005-11-30 | Method for preparing organosilyl quaternary ammonium salt sterilizing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100452940A CN1314320C (en) | 2005-11-30 | 2005-11-30 | Method for preparing organosilyl quaternary ammonium salt sterilizing agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1792158A CN1792158A (en) | 2006-06-28 |
| CN1314320C true CN1314320C (en) | 2007-05-09 |
Family
ID=36803958
Family Applications (1)
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|---|---|---|---|
| CNB2005100452940A Expired - Fee Related CN1314320C (en) | 2005-11-30 | 2005-11-30 | Method for preparing organosilyl quaternary ammonium salt sterilizing agent |
Country Status (1)
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|---|---|
| CN (1) | CN1314320C (en) |
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| US8304379B2 (en) * | 2007-07-25 | 2012-11-06 | Hiroshima University | Silicon compound-containing solidified detergent composition and method for producing the same |
| WO2010073825A1 (en) * | 2008-12-25 | 2010-07-01 | 国立大学法人広島大学 | Antibacterial composition and antiviral composition each containing silicon-containing compound, antibacterializing method, cleaning/mouth cleaning method, and method for immobilizing antibacterial agent or antiviral agent |
| CN102391299A (en) * | 2011-08-06 | 2012-03-28 | 江苏迅扬环保新材料有限公司 | Preparation method for organosilicon quaternary ammonium salt composite and application thereof |
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| CN104447845A (en) * | 2014-10-28 | 2015-03-25 | 南京睿友贸易实业有限公司 | Quaternary ammonium salt compound as well as preparation method and application thereof, antibacterial finishing agent and antibacterial fabrics |
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| CN111171798A (en) * | 2020-02-14 | 2020-05-19 | 东北石油大学 | Surface cationization silicon dioxide nano-particles |
| CN111424427A (en) * | 2020-04-28 | 2020-07-17 | 江苏惠兴康科技有限公司 | Non-dissolution type antibacterial finishing agent and preparation method thereof |
| CN113278029A (en) * | 2021-05-31 | 2021-08-20 | 杭州昕洋生物科技有限公司 | Double-branched-chain organosilicon quaternary ammonium salt and preparation method and application thereof |
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| US5135811A (en) * | 1986-02-04 | 1992-08-04 | Dow Corning Corporation | Polyamide yarn provided with a built-in antibacterial and method for its production |
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|---|---|
| CN1792158A (en) | 2006-06-28 |
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Assignee: Shandong Dayi Chemical Co., Ltd. Assignor: Shandong University Contract fulfillment period: 2009.6.30 to 2015.6.30 contract change Contract record no.: 2009370000288 Denomination of invention: Method for preparing organosilyl quaternary ammonium salt sterilizing agent Granted publication date: 20070509 License type: Exclusive license Record date: 2009.9.16 |
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Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2009.6.30 TO 2015.6.30; CHANGE OF CONTRACT Name of requester: SHANDONG DAYI CHEMICAL INDUSTRY CO., LTD. Effective date: 20090916 |
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Granted publication date: 20070509 Termination date: 20091230 |